4-Ethoxycarbonylphenylboronic acid → 4-(1-Benzoyl-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl)benzoic acid ethyl ester

HRID 659341Notes

Reaction equation

HRID 659341 reaction equation
I[C:2]1[CH:19]=[N:18][C:5]2[NH:6][CH2:7][CH2:8][N:9]([C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:11])[C:4]=2[CH:3]=1.[CH2:20]([O:22][C:23]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)=[O:24])[CH3:21]>>[CH2:20]([O:22][C:23](=[O:24])[C:25]1[CH:30]=[CH:29][C:28]([C:2]2[CH:19]=[N:18][C:5]3[NH:6][CH2:7][CH2:8][N:9]([C:10](=[O:11])[C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:4]=3[CH:3]=2)=[CH:27][CH:26]=1)[CH3:21]

Participants

3

Reactant 2

HCID 27343504-Ethoxycarbonylphenylboronic acidHCID 57886093(7-Iodo-3,4-dihydro-2H-pyrido[2,3-b]pyrazin-1-yl)phenylmethanone

Product 1

HCID 248527934-(1-Benzoyl-1,2,3,4-tetrahydropyrido[2,3-b]pyrazin-7-yl)benzoic acid ethyl esterYield 32%

Procedure

(7-Iodo-3,4-dihydro-2H-pyrido[2,3-b]pyrazin-1-yl)phenylmethanone (215 mg) was reacted with 4-ethoxycarbonyl phenyl boronic acid as in General Procedure 4A to give the title compound as an off-white solid (32% yield). M.p. 177-178° C., LCMS: m/z=388.23 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 1.38 t, (J=7.1 Hz, 3H), 3.67-3.72 (m, 2H), 4.01-4.08 (m, 2H), 4.36 (q, J=7.1 Hz, 2H), 5.21 (bs, 1H), 7.12-7.16 (m, 2H), 7.40-7.53 (m, 5H), 7.95 (d, J=8.3 Hz, 2H), 8.08 (s, 1H).

Sources & evidence

ORD record
ord-20dc8ecd2cfa451895ef7af16d3fb13e
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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